Compound 36
(R)-2-(4-methoxyphenethyl)octanal
From: Direct, enantioselective α-alkylation of aldehydes using simple olefins
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Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Prepared according to the general procedure outlined for compound 13. Purified by flash chromatography (2% Et2O/hexanes) using Davisil to provide the title compound (123 mg, 94% yield, 93% ee) as a colorless oil. Analytical data: [α]D22–1.5 (c = 1.00, CHCl3); 1H NMR (500 MHz, CDCl3) δ 9.58 (d, J = 2.9 Hz, 1H), 7.09 (d, J = 8.6 Hz, 2H), 6.83 (d, J = 8.6 Hz, 2H), 3.79 (s, 3H), 2.62–2.50 (m, 2H), 2.28 (dqd, J = 10.9, 5.4, 3.0 Hz, 1H), 1.98–1.89 (m, 1H), 1.75–1.62 (m, 2H), 1.52–1.44 (m, 1H), 1.27 (s, 8H), 0.87 (t, J = 6.9 Hz, 3H); 13C NMR (125 MHz, CDCl3) δ 205.5, 158.1, 133.7, 129.4, 114.0, 55.4, 51.4, 32.5, 31.8, 30.9, 29.5, 29.0, 27.1, 22.7, 14.2; HRMS (ESI+) Calcd. for C17H26O2+Na, 262.1933; Found, 262.1931; IR (thin film, cm-1) 2928, 2856, 1723, 1511, 1461, 1277, 1244, 1175, 1136, 1036, 822, 764, 750; HPLC analysis of the corresponding alcohol (OD, 3% IPA/Hexanes, 1.0 mL/min) indicates 93% ee: tR= 16.4 (minor), 17.4 (major) min.
